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. 1975 Sep;2(9):1539–1550. doi: 10.1093/nar/2.9.1539

Polynucleotides. XXXII. Further studies on the synthesis of oligonucleotides containing 8,2'-S-cycloadenosine.

M Ikehara, T Tezuka
PMCID: PMC343521  PMID: 170595

Abstract

A dinucleoside monophosphate, 8,2'-anhydro-8-mercapto-9-beta-D-arabinofuranosyladenine phosphoryl-(3'-5')-inosine (AspI) was synthesized by the condensation of protected 8-mercapto-adenosine 2',3'-cyclic phosphate and 2',3'-isopropylideneinosine with diphenylphosphorochloridate. 8-Mercaptoadenosine 2',3'-cyclic phosphate was polymerized by using tetraphenyl pyrophosphate as the condensing reagent. As oligonucleotides, thus obtained, contained some uncyclized 8-mercaptoadenosine residues and were cleaved at these sites with 0.3N KOH. As 5'-phosphate was synthesized and polymerized with DCC to give oligonucleotides with chain lengths 2 to 9.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Ikchara M., Tezuka T. Synthesis of cyclouridine oligonucleotides forming a double stranded complex of left-handedness with cycloadenosine oligonucleotides. J Am Chem Soc. 1973 Jun 13;95(12):4054–4056. doi: 10.1021/ja00793a041. [DOI] [PubMed] [Google Scholar]
  2. Ikehara M., Nagura T., Otsuka E. Polynucleotides. XXXI1. Synthesis of AUG analogs containing 8,2'-S-cycloadenosine, 8,5'-S-cycloadenosine, 8-bromoadenosin, 8-oxyadenosine and formycin in the first position of the codon. Nucleic Acids Res. 1975 Aug;2(8):1345–1363. doi: 10.1093/nar/2.8.1345. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Ikehara M., Tezuka T. Polynucleotides. XXVI. Complex formation of polynucleotides derived from formycin and laurusin with cyclonucleoside oligonucleotides. Nucleic Acids Res. 1974 Jul;1(7):907–917. doi: 10.1093/nar/1.7.907. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Ikehara M., Uesugi S. Polynucleotides. XVI. Oligomers of 8,2'-anhydro-8-mercapto-9-( -D-arabinofuranosyl)adennine 5'-monophosphate. J Am Chem Soc. 1972 Dec 27;94(26):9189–9193. doi: 10.1021/ja00781a033. [DOI] [PubMed] [Google Scholar]
  5. Nagyvary J., Provenzale R. G. Arabinonucleotides. I. A study of the formation of 3,-arabinonucleotidyl esters by the conversion of an internucleotide linkage. Biochemistry. 1969 Dec;8(12):4769–4775. doi: 10.1021/bi00840a018. [DOI] [PubMed] [Google Scholar]
  6. Provenzale R. G., Nagyvary J. Synthesis and structure of polyarabinouridylic acid. Biochemistry. 1970 Apr 14;9(8):1744–1752. doi: 10.1021/bi00810a013. [DOI] [PubMed] [Google Scholar]
  7. TOMLINSON R. V., TENER G. M. THE EFFECT OF UREA, FORMAMIDE, AND GLYCOLS ON THE SECONDARY BINDING FORCES IN THE ION-EXCHANGE CHROMATOGRAPHY OF POLYNUCLEOTIDES OF DEAE-CELLULOSE. Biochemistry. 1963 Jul-Aug;2:697–702. doi: 10.1021/bi00904a013. [DOI] [PubMed] [Google Scholar]
  8. Uesugi S., Yasumoto M., Ikehara M., Fang K. N., Ts'o P. O. Synthesis and properties of the dinucleoside monophosphate of adenine 8-thiocyclonucleoside. J Am Chem Soc. 1972 Jul 26;94(15):5480–5486. doi: 10.1021/ja00770a053. [DOI] [PubMed] [Google Scholar]
  9. YU C. T., ZAMECNIK P. C. A hydrolytic procedure for ribonucleosides and its possible application to the sequential degradation of RNA. Biochim Biophys Acta. 1960 Dec 4;45:148–154. doi: 10.1016/0006-3002(60)91435-9. [DOI] [PubMed] [Google Scholar]

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